Sodium Hydroxide → 7-(Trifluoromethyl)isoquinolin-1-amine

HRID 1896885Notes

Reaction equation

HRID 1896885 reaction equation
O([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:16]=2)[CH:11]=[CH:10][N:9]=1)C1C=CC=CC=1.C([O-])(=O)C.[NH4+:26].[OH-].[Na+]>O>[F:19][C:18]([F:21])([F:20])[C:15]1[CH:16]=[C:17]2[C:12]([CH:11]=[CH:10][N:9]=[C:8]2[NH2:26])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 517165Ammonium AcetateHCID 585624711-Phenoxy-7-(trifluoromethyl)isoquinoline

Product 1

HCID 585625367-(Trifluoromethyl)isoquinolin-1-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-phenoxy-7-(trifluoromethyl)isoquinoline (670 mg, 2.3 mmol), from above step D, and ammonium acetate (1.8 g, 23 mmol) was heated at 160° C. for 4 h. The mixture was cooled to room temperature and dissolved in water. Sodium hydroxide (1N solution) was added until the solution was basic and extracted with EtOAc (×4). The combined organic fractions were washed with saturated NaCl, dried over Na2SO4 and evaporated under vacuum to give the title compound.

Workup

  1. extractionextracted with EtOAc (×4)
  2. washThe combined organic fractions were washed with saturated NaCl
  3. dry with materialdried over Na2SO4
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-7a040232fffa41e298f7569d127a854f
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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